HCID 90280583, compound → HCID 90280652, compound

HRID 57757Notes

Reaction equation

HRID 57757 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:9]=[C:10]([C:17]2[C:18]([N+:37]([O-])=O)=[CH:19][C:20]3[O:24][C:23]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=3[CH:36]=2)[CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:37][C:18]1[C:17]([C:10]2[CH:9]=[C:8]([C:6](=[O:7])[NH:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:13]=[C:12]([NH2:14])[CH:11]=2)=[CH:36][C:21]2[C:22]([C:32]([NH:34][CH3:35])=[O:33])=[C:23]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[O:24][C:20]=2[CH:19]=1

Participants

4

Reactant 1

HCID 90280583HCID 90280583, compound

Product 1

HCID 90280652HCID 90280652, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(3-(tert-butylcarbamoyl)-5-nitrophenyl)-2-(4-fluorophenyl)-N-methyl-6-nitrobenzofuran-3-carboxamide (350 mg) in MeOH (50 mL) was added palladium on carbon (69.7 mg). The mixture was stirred under hydrogen with a balloon for 16 hours. Pd/C was removed by filtration and the filtrate was concentrated to give 6-amino-5-(3-amino-5-(tert-butylcarbamoyl)phenyl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide 3 (200 mg).

Workup

  1. customPd/C was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4694fb74668841fb8b55bceaa18d69b0
Source dataset
uspto-grants-2016_09
Patent number
US09434738B2

Reaction notes

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